Unreasonable Hospitality: Transforming Airbnb Rentals into Core Memories

If you’re a short-term rental owner or host, you might think of yourself first as a real estate investor. But the truth is: you’re in the hospitality business. You’re running a tiny, boutique hotel. And Unreasonable Hospitality offers incredible lessons on how going above and beyond can create unforgettable experiences for guests.

I first heard about this book through the Short-Term Rental Book Club. I’m part of two book clubs, one fiction club in my local community, and the virtual STR-focused one. To be honest, I’m not always the best member (sometimes I skim, sometimes I don’t finish, but I always show up for the discussion). One of the perks of the STR club is that they actually send you the book each month, which makes it so easy to dive right in.

I didn’t actually read Unreasonable Hospitality with the club. It wasn’t even on their list when I picked it up. I found a copy at the Level Up Your Listing Summit in March, squeezed it into my suitcase (after leaving behind some things at my Airbnb to make room), and started reading it on the plane home.

At first, I wasn’t hooked. The book dives into the restaurant industry, Will’s journey as a manager and later owner of a Michelin-starred restaurant, and I wasn’t sure how that tied into real estate. But the further I read, the more I realized how directly the lessons apply to us as short-term rental hosts.

Finding Nobility in Hospitality

One of the quotes that stopped me in my tracks was this:

“The moment you start to pursue service through a lens of hospitality, you understand there’s nobility in it. We do have the ability to make their lives better by creating a magical world they can escape to. And I see that not as an opportunity, but as a responsibility and a reason for pride.”

That line hit home. Even though what we provide as hosts is not a necessity, it still matters deeply. We’re creating escapes, memories, and experiences that people carry with them for a lifetime.

I’ve seen this firsthand. Guests have written in our property guestbooks thanking us for making it possible to spend Thanksgiving together after a military deployment. We’ve hosted baby showers where families came together to celebrate new life. One family even returns every August, year after year, after their old rental stopped accepting bookings. They originally came for the nearby amusement park, King’s Dominion, but ended up skipping it altogether just to enjoy time together at the house.

That’s the nobility of what we do. We’re not just renting a property; we’re creating the backdrop for someone’s core memory.

Adversity as Opportunity

Another standout line from the book:

“Adversity is a terrible thing to waste. All your well-laid plans go out the window, though it’s easy to panic. Creativity is the better solution.”

Will wrote this about running his restaurant through a recession, but the lesson applies to short-term rentals too.

I’ve had my fair share of challenges in this business. When we rented out our first North Carolina home long-term, tenants left it in awful condition—cat feces on the walls, mold in the fridge, holes in the drywall. It would have been easy to sell and walk away. Instead, we got creative, turned it into an Airbnb, and found success.

With our Kentucky property, the original plan was to use it as a wedding venue. Neighbors and zoning rules had other ideas. Once again, instead of giving up, we pivoted, reimagined it as a short-term rental, and it’s thriving today.

Even in day-to-day operations, adversity strikes. Once, we had a same-day check-in and check-out, only to discover two toilets completely clogged as one guest was leaving, just five hours before the next guest was set to arrive. It was stressful, yes, but it was also an opportunity to step up, respond quickly, and show both the plumber and our guests what it means to handle problems with grace.

Why Hospitality Requires Help

Hosting is a lot. Between guest communication, cleaning coordination, marketing, and everything else, it’s easy to feel overwhelmed. That’s why I love sharing not just inspiration but also practical ways to lighten the load.

I’ve been a superhost for over six years, across three states, with over 200 five-star reviews. I’ve co-hosted remotely, ensuring every guest had a seamless, five-star experience. Here at Brand & Market, we take a branding-first approach to property management because your rental isn’t just a property, it’s a brand, and it deserves to stand out.

Quotes That Challenge and Inspire

Towards the end of Unreasonable Hospitality, I found myself folding laundry while listening to the audiobook when three powerful quotes came one right after another. They were so impactful that I stopped, grabbed my notebook, and wrote them down.

1. “What would you try if you knew you couldn’t fail?”

This simple question hit me hard. I realized how often fear of failure holds me back, especially after our difficult experience in Kentucky. For a long time, I labeled that property as a failure, and that mindset has sometimes made me overly cautious when evaluating new investments.

But when I reframed it, asking myself what I would try if I knew I couldn’t fail. The possibilities opened wide. If failure wasn’t an option, I’d try all the things. And I want to encourage you, too: don’t let fear of failure stop you from pursuing your next big move.

2. “The opposite of a good idea is also a good idea.”

At first glance, this feels like a riddle. But in the context of hospitality, it makes perfect sense. Reasonable hospitality—clear check-in instructions, a standard welcome guide, basic cleanliness—is a good idea. But the opposite of that? Unreasonable hospitality, those over-the-top, unexpected touches, is also a good idea.

That’s what sets you apart. Reasonable hospitality is the baseline; unreasonable hospitality is the differentiator. It’s the reason guests remember your property and return year after year.

3. “A dream will never come true if you don’t say it out loud.”

This one cut deep for me. Back when we dreamed of turning our Kentucky property into a wedding venue, I shared that vision with anyone who would listen, including neighbors. I thought transparency and grace would win them over. Instead, pushback intensified, and eventually another venue nearby even adopted parts of our concept.

That experience made me retreat. I stopped putting dreams into the world, afraid of rejection or theft. But hearing this quote reminded me that silence won’t make dreams come true. So, I’m saying my dreams out loud here:

• By the end of this year, I want to sign two more co-hosting clients.
• Long-term, I dream of creating a micro resort on 5–10 acres, with shared amenities like a pool and sauna, and unique stays, a silo, a treehouse, a train car, each full of character. A little “island of misfits” where guests can connect, relax, and experience something unforgettable.

If you know of a property or want to collaborate on this vision, I’d love to talk.

4. “Hospitality is not transactional.”

Every interaction is part of a holistic guest experience. It’s not just about exchanging space for money. This is where intentionality matters. Curating experiences that go beyond the basics.

For example, at our Kentucky property, I created two bourbon trail itineraries: one for true connoisseurs and another for travelers who just want a fun, social experience. Both types of guests get what they came for, and both feel cared for in a personalized way. That’s unreasonable hospitality in action.

The Dream Weaver Concept

One of the most powerful ideas from Will’s book is the concept of “dream weavers.” At his restaurant, servers would listen closely to guest conversations and then take action to surprise them. If someone mentioned a movie they loved but hadn’t bought yet, a dream weaver would run out, buy the DVD, and gift it. If a guest worried about an expired parking meter during a four-hour meal, staff would slip out and feed the meter for them.

Over time, the restaurant built toolkits for common occasions, birthdays, anniversaries, promotions, so they were always prepared. And sometimes they went above and beyond in spectacular ways. One guest once mentioned wanting to try a specific New York hot dog but not having time before their flight. The restaurant sent a dream weaver to buy it, plated it like fine dining, and served it as part of their multi-course meal.

That’s unreasonable hospitality. Transforming small details into unforgettable moments.

For us as hosts, technology makes this even more achievable. Asking in your welcome message, “What brings you to town? Is there a special occasion?” opens the door to personalized touches. Maybe it’s as simple as sending a cake via DoorDash for a birthday or leaving a bottle of local wine for an anniversary.

Systems That Free You to Be Unreasonable

Of course, going above and beyond takes time and energy. That’s why having strong systems in place matters so much. I use property management software like Logify to automate the essentials: messaging cleaners, scheduling reminders, coordinating calendars. That automation frees me to focus on creativity and guest experience.

In other words, systems handle the reasonable so you can deliver the unreasonable. And it’s in that unreasonable space where five-star reviews are born.

Key Takeaways for Hosts

• Unreasonable hospitality is your differentiator. A clean house and nice furniture are important, but it’s the over-the-top details that transform a stay into a memory.
• Creativity over panic. Adversity will happen, plumbing emergencies, scheduling conflicts, but those moments are opportunities to show your excellence.
• Say your dreams out loud. They can’t take shape if you keep them hidden.
• Use systems to buy back your time. Automate the basics so you can invest energy into what truly matters: the guest experience.